Brewster
Walking Events Calendar near Brewster 2026-2027
Monthly updates for Brewster
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Explore the top walking events near Brewster for 2026-2027! We've gathered 69 great walks in the area. Check out our detailed list below to find your next local walk.
April 2027
May 2027
Walkers can choose 1 Mile, 5K, 10K, Half Marathon or Marathon routes across the historic Walkway Over the Hudson in the scenic Hudson Valley.
Walkers may lap a single and double track 2.2 mile loop with roots, rocks, rolling hills and 131 ft gain; pavilion aid and porta potties at 700 Peters Ln Stratford CT.
The untimed Fun Run/Walk of 3.1 Miles follows the Shepaug River through Steep Rock Preserve with a gradual incline. It starts at 2 Tunnel Road, Washington Depot CT; walkers will not receive a race bib.
MS Health Walk is based at Lewisboro Library in South Salem on village and road courses with parking at the library and online course maps, held alongside the race events.
Walk options 5K, 10K, 15K on looped course at Rockland Lake State Park Parking Lot #2, with start and finish at the same location alongside the running races.
June 2027
At Rockland Lake State Park, walkers can choose a flat, accessible 5K lake loop or a rugged 10K to Hook Mountain. The 5K is accessible with restrooms; the 10K is technical, 1,300 ft with cliffs and one aid station, no crew.